I’ve been in security for over 20 years now and have received thousands of emails asking for help or mentorship. And throughout that time I’ve also reached out to hundreds of people asking for something similar.
I’ve had a mix of success and failure on both ends of that equation, and I think I might have deciphered what was going wrong.
This can still work with some people, if it’s authentic.
I used to think it was all about the formal intro—like an old martial arts movie where a student seeks out the monk on the mountain. In that model, you start by talking about how you’re an unworthy worm, and how you could only hope to learn 1% of what they have to teach, and that would be more than enough…
That sounds humble and professional, and you’d think it’d be successful. But it’s actually a bad way to get a mentor, or even a response.
Rule #1 is to never give work to the customer.
The problem is that it violates several rules—most important of which is that if you’re asking a favor of someone, don’t give them work. Or at the very least, do as much of the work as possible and ask them if they’d be willing to do the final step.
Starstruck Padawan is not a strategy.
Here are some techniques that are likely get you a response, and maybe even a mentor, listed as a set of rules or guidelines.
1. Don’t overuse flattery
If you’re reaching out to someone to be your mentor there’s a chance they get a lot of email and a lot of pings on Twitter. And if that’s the case then they’ve probably had many people telling them how great they are as well.
Flattery tends to work best when it’s genuine and unexpected, not when the recipient hears it all the time from most everyone.
2. Ask something specific
The next thing to avoid is just saying hello and then not really saying anything. Few things are more annoying to people who get a lot of email than this.
They’ll also be annoyed that you forced them to be rude by annoying you.
Once again, if you do that, you’re then putting the burden on them to construct a conversation from scratch. They probably won’t. They’ll just ignore your email.
BAD: Hey I really respect your music career? Can you help me have a career like yours?
BETTER: Hello, I’ve always admired how you built your career over time. Is there a specific book that you’d recommend to yourself 20 years ago?
This is good because you’re limiting the work they have to do. If they have a book in mind, they might just respond and give you the title. But they’re not going to build you a custom career plan in response to the first option.
3. Behave like a future peer
The next thing to try to do is present yourself as an equal—albeit a very junior one. You can say things like, “I am building a career like yours”, or, “I have the same passion for plants that you do, so I intend to base my life around them the way you have.”
Don’t be discouraged if you get a very short email from someone. Even that is hard to do when you get hundreds a week.
And then follow that up with a specific observation, or insight, or question. This way they’re helping someone who is already on a path, not signing up to adopt someone. Far more people will respond to the former than the latter.
4. Show that you’ve done work already
This one does two things: it shows that you’re respectful of their time, and also that you’re willing to do work on your own. Nothing scares a mentor away faster than someone who wants the mentor to do all the work, and is waiting to have something handed to them.
You’d be surprised how many emails a person known in their field might get.
So instead of asking what books they recommend, ask,
This gives them the freedom to respond with anything ranging from, “No, I don’t.”, to “I haven’t read it yet.”, to a long response telling you why they hated it. And now you’re having a conversation.
5. Ask for an opinion on something you’ve created
The next level up (these are kind of getting more advanced as we go along) is to show them something you’ve made in your field, and ask for their opinion. Notice that this includes and builds upon several of the other points we’ve already made.
It starts with business, not flattery
You’re behaving like a peer by showing work in the field
And you’ve already created something
So that might start with something like:
This is golden. You’ve respected them without going off into flattery. You’ve acknowledged their work and the fact that you’ve put the work in to read it. And you’ve created something in the field like a future peer.
Unsupervised Learning — Security, Tech, and AI in 10 minutes…
Get a weekly breakdown of what's happening in security and tech—and why it matters.
And even though you’ve asked something of an open-ended question of “thoughts around it”, you’ve earned that a bit by all the previous points. Plus, they can respond with anything from an emoticon to an essay. This is a wonderful way to start a professional relationship.
6. Offer an improvement or adjustment to something they’ve made
And that brings us to the final level of communication to someone ahead of you in your craft—value add.
It’s one thing to make it easy for them to help you. And it’s another thing to show them something interesting. But what will really get their attention is if you help them in some way.
This hits all the previous points plus helps them actually improve! And if they respond they’re likely to move right into a peer-like relationship with you, even if you’re far more junior. This will make it easier to formally ask later for a mentorship, or to just maintain the relationship as is.
How to appear on a mentor’s radar
So there’s another aspect to this worth mentioning, which goes beyond just the initial contact email.
When you admire someone, there’s a tendency to try to forge a relationship with them and earn some measure of respect. That’s natural and great. But you can’t ask strangers for respect; you have to earn it.
To get noticed by someone significant, there’s no shortcut: you have to produce something significant.
You can’t really say,
It doesn’t work. I can tell you this—once again—from both sides of that mirror. I’ve been the person reaching out to someone I respect in that way, and I’ve been the person getting contacted. It fails in both.
Only one thing registers in the mind of someone like this is playing the game effectively. Producing noteworthy output. Registering on the value scale of the planet. Being significant in some way.
The more significant the person, the bigger the radar signature you’ll need.
You don’t have to produce at their level, but you have to provide value to others and be recognized for doing so. That is the single easiest way to earn respect from a prolific creator.
This isn’t about manipulation or trickery—it’s about respecting peoples’ time and attention. If you’re trying to manipulate someone, they will feel it.
Behave like a peer.
Indicate that you put the work in.
Show them something you’ve built.
Provide some kind of value to their craft.
If you seek respect, produce something they respect.
If you can do any of these—and avoid their opposites—you’ll significantly raise your chances of getting a response from your potential mentor. And if you can do all six you’ve maximized those chances.